Winding Oaks
Homes for Sale in Ocala, FL

Winding Oaks is a master-planned community under development on roughly 960 acres in southwest Ocala, Marion County, generally east of State Road 200 (SW College Road) and north of SW 80th Street, spanning ZIP codes 34474 and 34476. The land - one of Ocala's historic Thoroughbred horse farms and training centers - was assembled and entitled over about seven years, then purchased in July 2024 for nearly $32 million by KL Winding Oaks, LLC, an entity of The Kolter Group.

At full build-out the plan calls for approximately 2,028 single-family homes, 240 townhomes, and 888 multifamily units, plus about 270 acres of retail and commercial along the SR 200 frontage. D.R. Horton is the homebuilder, delivering ownership homes through named villages that are opening in phases: Tartan Farms at Winding Oaks, Mockingbird Reserve at Winding Oaks, and Derby Creek. The multifamily component is rental and falls outside owner-occupied scope; this page covers the for-sale single-family and townhome side.

The City of Ocala approved a Winding Oaks Community Development District (CDD) to finance more than $80.1 million in water, wastewater, roadway, and stormwater infrastructure. That means most Winding Oaks buyers will carry a CDD assessment in addition to any village homeowners-association dues - a normal structure for a plan this size, but one to price into the monthly rather than judge on base price alone. Planned amenities include a pool, clubhouse, fitness center, pickleball courts, a dog park, a playground, and trails that connect to a preserved historic horse cemetery on the property.

Because Winding Oaks is new, there is no resale track record under the community name yet, and figures such as final density, exact CDD assessment, and village-by-village HOA dues should be confirmed with the builder before acting. What is settled is location: the site sits about two miles from the SR 200 retail corridor and under five miles from Interstate 75, near the World Equestrian Center, historic downtown Ocala, and everyday shopping.

Pre-construction details are compiled from public records, builder announcements and builder listings, and are subject to change without notice; figures are deemed reliable but not guaranteed. Momentum Research figures are our own analysis. This page describes homes, pricing and community attributes, not residents.

Winding Oaks matters because of where it is and how big it is. The SR 200 corridor is southwest Ocala's primary growth axis - the spine that connects the World Equestrian Center area, the 34474/34476 retail cluster, and the I-75 interchange - and Winding Oaks drops one of the county's largest single land assemblies directly onto it. Roughly 270 acres of the plan are set aside for retail and commercial along that frontage, which is why nearby projects like a new BJ's Wholesale Club have been moving on the same stretch. For a buyer, that means shopping and services are being built into the plan rather than left a drive away.

The structure is a two-party model that is common for plans this size: The Kolter Group developed and entitled the land and stood up the infrastructure through the CDD, and D.R. Horton builds and sells the homes village by village. That is why you shop a village name - Tartan Farms, Mockingbird Reserve, or Derby Creek - rather than a single 'Winding Oaks' price list. Each village carries its own product line, lot sizes, and pricing, so the smart move is to compare them against each other inside the same master plan before comparing Winding Oaks to communities elsewhere in Ocala.

The equestrian heritage is more than marketing. The property was a working Thoroughbred farm and training center, and the plan preserves a historic horse cemetery with trail access - a genuine differentiator in a county that sells itself as the Horse Capital of the World. The trade-offs to weigh are the ones that come with any large, actively-building master plan: construction traffic and phasing while the community fills in, a CDD assessment funding that $80 million-plus of infrastructure, and amenities that are delivered over time rather than all at once. None of those are red flags on their own - they are simply the cost and timeline of buying early into a plan that is still taking shape.

Most listings for a plan this new either bury the CDD or quote a base price as if it were the whole story. This page is built from the public record - Kolter's land purchase and CDD filing, the approved unit counts and infrastructure figure, and D.R. Horton's own village listings - and it says plainly what is settled versus what a buyer still has to confirm: the exact CDD assessment, each village's HOA dues, gating, and final density. No automated valuation, no guaranteed-appreciation claims, and no pretending an early-phase master plan has a resale history it has not earned yet. When you are ready, we will pull the current, address-specific numbers for the village and plan you are actually considering.

Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.